


Mr. Hale's Babysitter

by SinQueen69



Series: Requests [95]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Babysitter Stiles Stilinski, Creampie, Derek Hale Has a Big Dick, Dirty Talk, Don't copy to another site, Loss of Virginity, M/M, Prompt Fill, Rough Sex, Single Parent Derek Hale, Teen Stiles Stilinski, Underage - Freeform
Language: English
Status: Completed
Published: 2020-09-20
Updated: 2020-09-20
Packaged: 2021-03-08 00:47:08
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,131
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26566786
Author URL: https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69
Summary: Request Anon’sDerek Hale/Stiles Stilinski. Stiles asks to borrow a condom from Derek, but he finds out Derek’s are XXL and Derek convinces Stiles that a high schooler can’t give him what he needs, a nice big dick filling him up. But Derek can ;)+Stiles/Derek Underage!Stiles is babysitting SingleParent!Derek's kid and Stiles fingers himself in Derek's bed while the kid is asleep but Derek comes home and shows Stiles how being fucked really feels like
Relationships: Derek Hale/Stiles Stilinski
Series: Requests [95]
Series URL: https://archiveofourown.org/series/1618726
Comments: 10
Kudos: 686





	Mr. Hale's Babysitter

Stiles had honestly not meant to see the box of condom’s but he was looking for wipes in the bathroom to clean up some of the paint Dean had managed to get everywhere during their art time. Instead of finding a box of wipes, Stiles had pulled out a half-empty condom box and his eyes went wide when he saw the sizing proclaimed in large print on the side.

XXL.

Stiles’ cock twitched in his jeans and his cheeks burned as a mental image of Mr. Hale’s cock size appeared in his mind. Stiles dropped the condom box on the counter as he grabbed the wipes and hurried out of the bathroom. He didn’t think about it again until he was sprawled out on Mr. Hale’s bed, staring at the ceiling. Dean had finally fallen asleep down the hall and he was exhausted. Mr. Hale had told him to use his bed if he needed a rest, as they didn’t have a spare room in their small house. 

Laying in Mr. Hale’s bed the condom box and the XXL sizing popped back into the teen’s mind and his jeans started to tent. Stiles moaned as he cupped himself through his jeans, rubbing at his hardening cock as he conjured up a mental image of the older man. 

Stiles wiggled out of his jeans and boxers before he could process what he was doing and sucked messily on his fingers. Stiles planted his feet on the end of the bed, rubbing his wet fingers over his hole as he covered his mouth with his free hand as not to wake the sleeping child down the hall as he worked his finger into his ass. 

Stiles panted and squirmed as he imagined the large, thick cock that would jut up from Mr. Hale’s groin, he imaged how damn good it would feel inside of his virgin hole. Stiles had seen his fair share of cocks in the locker room and no way any of them could fit the XXL condom’s Mr. Hale had in his bathroom. Stiles worked his fingers in and of his hole desperately, aching to be filled by the older man’s thick cock. 

“This is quite a nice sight to come home to,” Mr. Hale’s deep voice rang out and Stiles jolted as he sat upon said man’s bed, but this just forced Stiles’ fingers deeper into his ass and Stiles moaned in bliss when his fingers pressed against his prostate. 

“Don’t stop on my account Stiles,” Mr. Hale was taking off his jacket, eyes dark, as they stayed trained on the half-naked teen fingering himself in his bed. 

“Mr. Hale, I can explain, ahh,” Stiles cut himself off with a whine when the older man stepped up to the bed and pushed him flat on his back with a hand to his chest. 

“I noticed that you found my condom’s, of course, you were interested. No one your age will be able to compare, I bet your aching to be filled with my fat cock,” Mr. Hale tugged his tie loose around his neck as he pushed Stiles shirt up to his neck, rubbing his thumb over one of the teen’s pink nipples. Stiles keened and curled his fingers inside of himself as his cock drooled against his now bare stomach. 

“How about instead of your usual payment, I fuck you with my cock and we call it even.” Mr. Hale suggested as he trailed a calloused finger down Stiles’ shaft, grinning sharply at the way Stiles arched into his touch. 

“Yes, fuck, yes!” Stiles eagerly agreed, slapping his hand over his mouth again to muffle his moan when the older man unzipped his suit pants, allowing his thick, veined cock to pop free. Stiles had never seen one so big and he had no doubts that the man could fill the XXL condoms with no problem. 

“Think you can handle it?” Mr. Hale asked cockily as he grasped his cock and slapped it against Stiles’ ass lewdly. 

“Fuck I want it so badly Mr. Hale,” Stiles pulled his fingers out of his ass and held his ass cheeks apart to show the older man his pink, puffy hole. 

“If I had known you were such a slut I could have saved some money,” Mr. Hale chuckled as he suddenly grabbed Stiles’ by his hips and flipped him onto his front and yanked his hips up. 

Stiles squealed at the easy way the older man positioned him the way he wanted, he spread his legs wider as he heard the sound of lube being spread on skin. Stiles’ heart was pounding in his chest as the slick, blunt head of Mr. Hale’s cock pressed against his hole. 

“You’re going to feel my cock for days,” Mr. Hale promised in a low, husky voice that had Stiles shivering. Stiles buried his face in the pillow beneath his face and bit into the fabric to muffle his cry as the older man pushed his massive cock into him. 

“Mm, yeah, that’s real good Stiles.” Mr. Hale sounded breathless and pleased as his large balls settled against the teen’s upturned ass. Stiles’ hole was extremely tight, all but clinging to his cock and it felt so damn hot around his cock.

Mr. Hale licked his lips at the sight of Stiles’ trembling as his young body adjusted to all but being split open on the older man’s cock. It was quite the sight and he couldn’t help but start to fuck into the teen earnestly. 

Stiles whined and mewled, as he was helpless when the older man started thrusting into him, he felt so full that he could feel it in his throat. It was mind-numbing and wonderful, Stiles’ wanted more. Stiles lay on the bed; gasping and keening as he was fucked wide open by Mr. Hale’s massive cock, spots appearing his vision each time the man was fully sheathed inside of him right against his prostate.

Stiles had to bit down on the pillow again as he shook apart on the older man’s cock as he came untouched, soiling the sheets below his hips. Stiles panted and whimpered as the older man fucked him harder if that was even possible before Stiles’ arched and his eyes rolled up into his head when he felt a burst of warmth inside of him as Mr. Hale moaned lowly. Stiles felt wrung out and well used as Mr. Hale slipped out of his ass, a trail of cum following and Stiles’ eyes slipped shut. 

“Don’t worry Stiles, I’ll call your dad and tell him you're spending the night here,” Mr. Hale sounded amused as he patted Stiles’ head as the teen passed out, completely exhausted in a way he had never been before.

**Author's Note:**

> Check Out My Twitter & Curious Cat
> 
> Twitter.com/sinqueen69  
> https://curiouscat.qa/SinQueen69


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